Rearrangement and trans-elimination against the chugaev reaction rule

✍ Scribed by T. Taguchi; Y. Kawazoe; K. Yoshihira; H. Kanayama; M. Mori; K. Tabata; K. Harano

• Book ID: 104250011
• Publisher: Elsevier Science
• Year: 1965
• Tongue: French
• Weight: 262 KB
• Volume: 6
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99531-0

✦ Synopsis

In the foregoing papers (2,3), it was reported that dialkylaminoalkyl S-alkyl xanthntes thermally rearrange to dialkylaminoalkyl alkyl dithiolcarbonates with or without shift of the dialkylamino group.

The general feature of the rearrangement is that .it requires antiparallel coplanarity of the xanthate group with the dialkylamino group, where the latter group can anchimerically work on the carbon atom holding the former.